反应详情

温度

80 °C

1-Trifluoromethylsulphonylcyclohex-1-ene (3 g, 13 mmol), cesium carbonate (8.4 g, 26 mmol) and 2,5-difluorophenyl boronic acid (2.88 g, 18 mmol) were dissolved in dimethoxyethane/water [9:1] (200 ml). The flask was degassed and then tetrakistriphenylphosphine palladium (125 mg) was added, the mixture warmed to 80° C. over 4 hr and then cooled to r.t. The solution was filtered through Celite™, diluted with water (20 ml) and the solution washed with ethyl acetate (2×100 ml). The organic phase washed with brine (100 ml), dried (MgSO4) and evaporated. The clear oil obtained was purified by column chromatography on silica gel eluting with hexanes, to give 1-(2,5-difluorophenyl)cyclohex-1-ene. 1H NMR (CDCl3) 6.97-6.73 (3H, m), 5.97-5.96 (1H, m), 2.35-2.31 (2H, m), 2.23-2.14 (2H, m) and 1.79-1.68 (1H, m).

1. customThe flask was degassed
2. additiontetrakistriphenylphosphine palladium (125 mg) was added
3. temperaturecooled to r.t
4. filtrationThe solution was filtered through Celite™
5. additiondiluted with water (20 ml)
6. washthe solution washed with ethyl acetate (2×100 ml)
7. washThe organic phase washed with brine (100 ml)
8. dry with materialdried (MgSO4)
9. customevaporated
10. customThe clear oil obtained
11. customwas purified by column chromatography on silica gel eluting with hexanes